nta trans here you did your best to be accommodating and in terms of transitioning late it can cause issues as you said with the sizing also as blunt as i can be about being trans personally i think its best to wait before for your body to change before starting to go out in public for well safety and so you dont get a bunch of weird stares comments etc just my opinion though i hope their transitions going alright because ik it can be bad for some when they transition that late